Production of organic sulphur compounds



Patented Dec. .28, 19357 2,103,879 PRODUCTION OF ORGANIC SULPHUR COM- POUNDS Hanns Ufer, Ludwigshalen-on-the-Rhine, Ger-- many, assignor to I. G. Farbenindustrie Aktiengesellschaft, Frankfort-on-the-Main, Germany No Drawing. Application November 22, 1935,

Serial No. 51,081. 1934 In Germany December 1'7,

8 Claims. (Cl. 260158) This invention relates to the production of organic sulphur compounds.

I have now found that valuable organic sulphur compounds are obtained by causing vinyl sulpound dissolves well in water, somewhat in the same way as soap; it is difflculty soluble in cold ethanol and readily soluble in hot ethanol.

Corresponding compounds are obtained with other vinyl'alkyl sulphones, as for example with octodecyl or oleyl vinyl sulphone, and the mixcohol.

5 phones having the general formula t f 1 1k 1 I h ures o vmy a y sup ones such as may be R(SOZ C H=CH2)I obtained for example from various alcohols of in whichR is a saturated or unsaturated aliphatic high mo ecula Weight, h as t e mixtures of radiclecontaining at least 7 carbon atoms and a: alcohols n le y the lytic hydrogena- 10 1 awhole number t react t bisulphites of tion of the fatty acids derived from fats or oils 10 light metals, such as sodium, potassium or calof al or vegetable ori cium.

The vinyl sulphones employed as starting ma- Emma 18 2 terials are for example obtainable by reacting the A m xture f 53 Parts of oCtOdBCYIViHYI corresponding vinyl sulphides with peroxidic oxiphone a d 100 P t of a 40 P Cent q us so- 15 dizmg agents or hypochlorites under mild lution of sodium bisulphite is heated for about 4 dmons. v hours at a temperature of between 80 and 95 0., Among the aliphatic vinyl sulphones which may I While vigorously stirring- After -Cooling the y be used in the present process may be mentio d tals formed are filtered off by suction and pressed go for example heptyl, dodecyl, octodecyl and oleyl onto ll- The de reaction pr duct thus ch- 20 vinyl sulphones. Vinyl sulphones which contain tamed i purified by Washing with ether and then t vinyl sulphone-group more th once i th recrystallized from alcohol. Colorless crystals molecule, as for example 1,12-divinyl sulphone are obtained, he p i n f which correoctodecane, may be caused to react a correspondsponds to the formula C1aHa7SOzCH2CHzSOaNa :5 ing number of times.- The vinyl alkyl sulphones d w i a e decomposedn being heated may also have branched chains and may contain above 225 C. other atoms or atomic groups, as for example In the s manner oleyl Vinyl sulphone can halogen atoms or hydroxyl,a lkoxyl,hydroxyalkyl, be reacted with sodium bisulphite. when emnitro, amino, sulph-hydryl, carboxyl or sulphonic P y ng po ass m r calcium i ph instead acidgroups, of sodium bisulphite the potassium or calcium 30 During the reaction, which is preferably carsalts of the said alkyl sulphone ethane sulphonic ried out in the presence of solvents or diluents' acids are obtained. such as water or aqueous alcohol and if desired What I claim is:- under pressure, the bisulphite'adds onto the vinyl The P s of producing ganic sulphur s5 sulphone groups with the formation of sulphonic mp n whi comprises rea tin vinyl sul- B5 acid salts, phones having the general formula The compounds obtained according to this invention may be employed in particular as assist- R(SO2 CH=CH2) v ants for the textile and related industries. in which R is an aliphatic radicle containing at 40 The following examples will further illustrate least 7 carbon atoms and a: is a whole number, 4 how the present. invention may be carried out with bisulphites of light metals selected from the in practice but the invention is not restricted to group consisting of sodium, potassium and calthese examples. The parts are by weight. cium.

- 2. The process of producing organic sulphu Example 1 compounds which comprises reacting vinyl sul- 45 A mixture of 60 parts of dodecyl vinyl sulphones having the general formula phone and 300.parts of a from 38 to 40 per cent solution of sodium bisulphite is stirred for about R(sO2 CH=CH2) Seven hours t about Aftel cooling, the in which R is an aliphatic radicle containing at colorless crystal p lp is separated from the least 7 carbon atoms and a: is a whole number, 50 mother qu a d ta l d f m wat r. 00 with bisulphites of light metals'selected from ,the orless crystals are obtained the composition of group consisting of sodium, potassium and calwhich probably corresponds to the formula cium inthe presence of a diluent selected from CH3(CH2)11SO2CH2CHzSOaNa. The new comthe group consisting of water and aqueous al- 3. The process of producing organic sulphur compounds which comprises reacting vinyl sulphones having the general formula in which R is an aliphatic radicle' containing at least '7 carbon atoms and a: is a whole number, with bisulphites of light metals selected from the group consisting of sodium, potassium and calcium in the presence of water.

4. The process of producing organic sulphur compounds which comprises reacting vinyl sul phones having the general formula R(So2-CH=CH2)::

in which R is an aliphatic radicle containing at least 7 carbon atoms and m is a. whole number. with bisulphites or light metals selected from the group consisting of sodium, potassium and calcium in the presence 01' aqueous alcohol.

5. Alkyl-sulphone-ethyl-sulphonic acid salts of light metals selected from the group consisting of sodium, potasium and calcium, the alkyl group of which contains at least 7 carbon atoms.

6. Dodecyl-sulphone-ethyl-sulphonic acid sodium salt.

7. Octodecyl-sulphone-ethyl-sulphonic acid sodium salt.

8. Oleyl-sulphone-ethylsulphonic acid sodium salt.

HANNS 

